Boron containing heterocyclic compounds

Claim 2

A compound having the formula: ##STR6## where R is hydrogen or an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 24 carbon atoms, R 1 and R 4 are the same or different radicals selected from hydrogen or alkyl, aryl, alkylaryl or arylalkyl radicals or a mixture thereof, said radicals having from 1 to about 30 carbon atoms, R 2 and R 3 are the same or different aryl, alkylaryl or arylalkyl radicals having from about 6 to about 30 carbon atoms, R 5 , R 6 , R 7 , and R 8 are the same or different radicals selected from hydrogen or an alkyl radical having from 1 to about 6 carbon atoms, Y is an integer between 1 and 4, and X is hydrogen or a metal selected from a transition metal having an atomic number of 21 through 30 or a Group IVA metal.

Claim 3

A compound having the formula: ##STR7## where R is an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 24 carbon atoms, R 1 , and R 4 are the same or different radicals selected from hydrogen or an alkyl, aryl, alkylaryl or arylalkyl radicals having from 1 to about 30 carbon atoms, R 2 and R 3 are the same or different aryl, alkylaryl or arylalkyl radicals having from about 6 to about 30 carbon atoms, R 5 , R 6 , R 7 and R 8 are the same or different radicals selected from hydrogen or an alkyl radical having from 1 to about 6 carbon atoms, Y is an integer between 1 and 4, and X is hydrogen or a metal selected from a transition metal having an atomic number of 21 through 30 or a Group IVA metal.

Claim 4

A compound having the formula: ##STR7## where R is an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 24 carbon atoms, R 1 , and R 4 are the same or different radicals selected from hydrogen or an alkyl, aryl, alkylaryl or arylalkyl radicals having from 1 to about 30 carbon atoms, R 2 and R 3 are the same or different aryl, alkylaryl or arylalkyl radicals having from about 6 to about 30 carbon atoms, R 5 , R 6 , R 7 and R 8 are the same or different radicals selected from hydrogen or an alkyl radical having from 1 to about 6 carbon atoms, Y is an integer between 1 and 4, and X is hydrogen or a metal selected from a transition metal having an atomic number of 21 through 30 or a Group IVA metal.

Claim 5

The compound defined in claim 2 wherein R is an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 18 carbon atoms.

Claim 6

The compound defined in claim 2 or 3 wherein R 1 and R 4 are the same or different radicals selected from hydrogen or alkyl, aryl, alkylaryl or arylalkyl radicals having from 1 to about 20 carbon atoms, and R 2 and R 3 are aryl or arylalkyl radicals having from about 6 to about 20 carbon atoms.

Claim 7

The compound defined in claims 2 or 3 wherein R 2 and R 3 are the same aryl radical having 6 carbon atoms.

Claim 8

The compound defined in claims 1 or 2 wherein X is a metal selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, tin and lead and mixtures thereof.

Claim 9

The compound defined in claims 1 or 2 wherein said compound contains from about 0.5 to about 10 weight percent of boron.

Claim 10

The compound defined in claims 1 or 2 wherein said compound contains from about 1 to about 17 weight percent of a transition metal having an atomic number from 21 to 30 or a Group IVA metal.

Claim 11

A process for producing a boron-containing heterocyclic compound having the formula: ##STR8## where R is hydrogen or an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 24 carbon atoms, R 1 and R 4 are the same or different radicals selected from hydrogen or alkyl, aryl, alkylaryl or arylalkyl radicals having from 1 to about 30 carbon atoms, R 2 and R 3 are the same or different aryl, alkylaryl or arylalkyl radicals having from about 6 to about 30 carbon atoms, R 5 , R 6 , R 7 , and R 8 are the same or different radicals selected from hydrogen or an alkyl radical having from 1 to about 6 carbon atoms, Y is an integer between 1 and 4, and X is hydrogen or a metal selected from a transition metal having an atomic number of 21 through 30 or a Group IVA metal, which comprises: (A) contacting a primary amine or ammonia with an aromatic oxide of the formula: ##STR9## wherein at least one of said R 1 ', R 2 ', R 3 ' or R 4 ' is aryl, alkylaryl or arylalkyl with the remaining R groups being independently hydrogen or an organic radical having 1 to 30 carbon atoms to produce a reaction product; and (B) contacting the reaction product of step (A) with boric acid to produce said boron-containing heterocyclic compound.

Claim 12

A process for producing a boron-containing heterocyclic compound having the formula: ##STR8## where R is hydrogen or an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 24 carbon atoms, R 1 and R 4 are the same or different radicals selected from hydrogen or alkyl, aryl, alkylaryl or arylalkyl radicals having from 1 to about 30 carbon atoms, R 2 and R 3 are the same or different aryl, alkylaryl or arylalkyl radicals having from about 6 to about 30 carbon atoms, R 5 , R 6 , R 7 , and R 8 are the same or different radicals selected from hydrogen or an alkyl radical having from 1 to about 6 carbon atoms, Y is an integer between 1 and 4, and X is hydrogen or a metal selected from a transition metal having an atomic number of 21 through 30 or a Group IVA metal, which comprises: (A) contacting a primary amine or ammonia with an aromatic oxide of the formula: ##STR9## wherein at least one of said R 1 ', R 2 ', R 3 ' or R 4 ' is aryl, alkylaryl or arylalkyl with the remaining R groups being independently hydrogen or an organic radical having 1 to 30 carbon atoms to produce a reaction product; and (B) contacting the reaction product of step (A) with boric acid to produce said boron-containing heterocyclic compound.

Claim 13

The process defined in claim 9 wherein the contacting in step (A) is with a primary amine selected from the group consisting of methylamine, ethylamine, propylamine, butylamine, octadecylamine, cyclohexylamine, dodecylamine, phenylamine, oleylamine, cocoamine and tallowamine and mixtures thereof.

Claim 14

The process defined in claim 9 wherein the aromatic oxide is a member selected from the group consisting of styrene oxide, alpha methyl styrene oxide, para tertiary butyl styrene oxide, ortho methyl styrene oxide and para methyl styrene oxide and mixtures thereof.

Claim 15

The process defined in claim 9 wherein a primary amine and an aromatic oxide are contacted in step (A) at a molar ratio of 1:2 to produce said reaction product.

Claim 16

The process defined in claim 9 wherein the reaction product and boric acid are contacted at a molar ratio of from 1:2 to 1:1 to produce a boron containing heterocyclic compound.

Claim 17

The process defined in claim 13, including contacting the boron containing heterocyclic compound with a metal selected from either a transition metal having an atomic number of 21 to 30 or a Group IVA metal or a mixture thereof.

Claim 18

The process defined in claim 14 wherein the transition metal or Group IVA metal is a member selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, tin and lead and mixtures thereof.

Claim 19

The process defined in claim 14 wherein the boron-containing heterocyclic compound and the metal are contacted at a molar ratio of from about 1:4 to about 6:1.

Claim 20

The process defined in claim 14 wherein the boron-containing heterocyclic compound and metal are contacted at a temperature of from about 176° F. to about 450° F. and a pressure of from atmospheric pressure to about 500 p.s.i.g.

Claim 21

A process for producing a boron-containing heterocyclic compound having the formula: ##STR10## where R is an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 24 carbon atoms, R 1 and R 4 are the same or different radicals selected from hydrogen or alkyl radicals having from 1 to about 6 carbon atoms, R 2 and R 3 are the same or different aryl, alkylaryl or arylalkyl radicals having from 6 to about 30 carbon atoms, R 5 , R 6 , R 7 , and R 8 are the same or different radicals selected from hydrogen or an alkyl radical having from 1 to about 6 carbon atoms, Y is an integer between 1 and 4, and X is hydrogen or a metal selected from a transition metal having an atomic number of 21 through 30 or a Group IVA metal, which comprises: (A) contacting a primary amine with an aromatic oxide of the formula: ##STR11## wherein at least one of said R 1 ', R 2 ', R 3 ' or R 4 ' is aryl, alkylaryl or arylalkyl with the remaining R groups being independently hydrogen or an alkyl radical having 1 to 6 carbon atoms to produce a reaction product; and (B) contacting the reaction product of step (A) with boric acid to produce said boron-containing heterocyclic compound.

Claim 22

A process for producing a boron-containing heterocyclic compound having the formula: ##STR10## where R is an alkyl, alkene, alkadiene, aryl, alkylaryl or arylalkyl radical having from 1 to about 24 carbon atoms, R 1 and R 4 are the same or different radicals selected from hydrogen or alkyl radicals having from 1 to about 6 carbon atoms, R 2 and R 3 are the same or different aryl, alkylaryl or arylalkyl radicals having from 6 to about 30 carbon atoms, R 5 , R 6 , R 7 , and R 8 are the same or different radicals selected from hydrogen or an alkyl radical having from 1 to about 6 carbon atoms, Y is an integer between 1 and 4, and X is hydrogen or a metal selected from a transition metal having an atomic number of 21 through 30 or a Group IVA metal, which comprises: (A) contacting a primary amine with an aromatic oxide of the formula: ##STR11## wherein at least one of said R 1 ', R 2 ', R 3 ' or R 4 ' is aryl, alkylaryl or arylalkyl with the remaining R groups being independently hydrogen or an alkyl radical having 1 to 6 carbon atoms to produce a reaction product; and (B) contacting the reaction product of step (A) with boric acid to produce said boron-containing heterocyclic compound.

Claim 23

The process defined in claim 10, 12, 13, 14, 15, 16 or 18 wherein the aromatic oxide comprises styrene oxide.

Claim 24

The process defined in claim 18 wherein the aromatic oxide is a member selected from the group consisting of styrene oxide, alpha methyl styrene oxide, para tertiary butyl styrene oxide, ortho methyl styrene oxide and para methyl styrene oxide and mixtures thereof.

Claim 25

The process defined in claim 18, including the further step of contacting the boron-containing heterocyclic compound with a metal selected from either a transition metal having an atomic number of 21 to 30 or a Group IVA metal and mixtures thereof.

Claim 26

The process defined in claim 21 wherein the transition metal or Group IVA metal is a member selected from the group consisting of scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, tin and lead or a mixture thereof.

Claim 27

The process defined in claim 21 wherein the boron containing heterocyclic compound and the metal are contacted at a molar ratio of from 1:4 to 6:1.

Claim 28

The process defined in claim 21 wherein the boron-containing heterocyclic compound and metal are contacted at 176° F. to about 450° F. and a pressure of from atmospheric pressure to about 500 p.s.i.g.